Add configurable fingerprints and MACCS keys

Cargo.toml

@@ -1,7 +1,7 @@
 [package]
 name = "rdkit"
 version = "0.4.12"
-edition = "2021"
+edition = "2024"
 authors = ["Xavier Lange <xrlange@gmail.com>", "Javier Pineda <javierjpineda13@gmail.com"]
 license = "MIT"
 description = "High level RDKit functionality for rust"
@@ -17,7 +17,7 @@ cxx = "1"
 flate2 = "1"
 log = "0.4"
 rdkit-sys = { path = "rdkit-sys", version = "0.4.9" }
-thiserror = "1"
+thiserror = "2"
 
 [dev-dependencies]
-env_logger = "0.9.0"
+env_logger = "0.11"

README.md

@@ -2,7 +2,7 @@ RDKit
 ---
 
 A high-level library for performing common RDKit tasks such as SMILES parsing, molecule normalization, etc. Uses
-the C++ API via bindings from [rdkit-sys](https://crates.io/crate/rdkit-sys).
+the C++ API via bindings from [rdkit-sys](https://crates.io/crates/rdkit-sys).
 
 Notice: Requires rdkit 2023.09.1 or higher (like Ubuntu Noble 24.04)
 

benches/atom_iteration_benchmark.rs

@@ -0,0 +1,102 @@
+#![allow(soft_unstable)]
+#![feature(test)]
+extern crate test;
+
+use rdkit::ROMol;
+
+/// Drug-like molecules of varying size for realistic benchmarking.
+/// These cover common pharmaceutical scaffolds and natural products.
+const SMILES_SET: &[&str] = &[
+    // aspirin
+    "CC(=O)Oc1ccccc1C(=O)O",
+    // ibuprofen
+    "CC(C)Cc1ccc(cc1)C(C)C(=O)O",
+    // caffeine
+    "Cn1c(=O)c2c(ncn2C)n(C)c1=O",
+    // diazepam
+    "O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1C",
+    // atorvastatin (lipitor)
+    "CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O",
+    // taxol core
+    "CC1=C2C(OC(=O)c3ccccc3)C(O)C4(OC(=O)C(O)(CC(OC(=O)c5ccccc5)C1O)C24C)C(=O)c1ccc(OC)cc1",
+    // vancomycin fragment
+    "OC1C(O)C(OC2C(O)C(O)C(O)C(CO)O2)OC(CO)C1NC(=O)C1CC(O)CN1C(=O)C(NC(=O)C1CC(=O)NC(=O)C1O)C(O)c1ccc(O)cc1",
+];
+
+/// Baseline: SMILES parsing cost.
+#[bench]
+fn bench_parse_smiles(b: &mut test::bench::Bencher) {
+    b.iter(|| {
+        for smiles in SMILES_SET {
+            test::black_box(ROMol::from_smiles(smiles).unwrap());
+        }
+    });
+}
+
+/// Iterate all atoms via atom_ref (&self), read 7 properties per atom.
+/// This is the realistic featurization workload.
+#[bench]
+fn bench_atom_ref_all_properties(b: &mut test::bench::Bencher) {
+    let mols: Vec<ROMol> = SMILES_SET
+        .iter()
+        .map(|s| ROMol::from_smiles(s).unwrap())
+        .collect();
+
+    b.iter(|| {
+        for mol in &mols {
+            let n = mol.num_atoms(true);
+            for i in 0..n {
+                let atom = mol.atom_ref(i);
+                test::black_box(atom.symbol());
+                test::black_box(atom.get_atomic_num());
+                test::black_box(atom.get_formal_charge());
+                test::black_box(atom.get_is_aromatic());
+                test::black_box(atom.get_hybridization_type());
+                test::black_box(atom.get_degree());
+                test::black_box(atom.get_total_num_hs());
+            }
+        }
+    });
+}
+
+/// Same workload via atom_with_idx (&mut self).
+/// Regression guard: should be the same speed as atom_ref.
+#[bench]
+fn bench_atom_mut_all_properties(b: &mut test::bench::Bencher) {
+    let mut mols: Vec<ROMol> = SMILES_SET
+        .iter()
+        .map(|s| ROMol::from_smiles(s).unwrap())
+        .collect();
+
+    b.iter(|| {
+        for mol in &mut mols {
+            let n = mol.num_atoms(true);
+            for i in 0..n {
+                let atom = mol.atom_with_idx(i);
+                test::black_box(atom.symbol());
+                test::black_box(atom.get_atomic_num());
+                test::black_box(atom.get_formal_charge());
+                test::black_box(atom.get_is_aromatic());
+                test::black_box(atom.get_hybridization_type());
+                test::black_box(atom.get_degree());
+                test::black_box(atom.get_total_num_hs());
+            }
+        }
+    });
+}
+
+/// Clone cost alone. Useful for understanding the cost of cloning
+/// molecules when only &ROMol is available but mutation is needed.
+#[bench]
+fn bench_clone_molecules(b: &mut test::bench::Bencher) {
+    let mols: Vec<ROMol> = SMILES_SET
+        .iter()
+        .map(|s| ROMol::from_smiles(s).unwrap())
+        .collect();
+
+    b.iter(|| {
+        for mol in &mols {
+            test::black_box(mol.clone());
+        }
+    });
+}

rdkit-sys/Cargo.toml

@@ -2,7 +2,7 @@
 name = "rdkit-sys"
 authors = ["Xavier Lange (xrlange@gmail.com)", "chrissly31415"]
 version = "0.4.12"
-edition = "2021"
+edition = "2024"
 license = "MIT"
 description = "RDKit CFFI library builder and bindings"
 repository = "https://github.com/rdkit-rs/rdkit/tree/main/rdkit-sys"
@@ -14,9 +14,9 @@ exclude = ["rdkit-*", "*.tar.gz", "examples/"]
 cxx = "1.0.109"
 
 [build-dependencies]
-env_logger = "0.10.0"
+env_logger = "0.11"
 cxx-build = "1.0.109"
-which = "4.4.2"
+which = "8"
 
 [features]
 default = []

rdkit-sys/build.rs

@@ -1,4 +1,4 @@
-const CPP_VERSION_FLAG: &str = "-std=c++17";
+const CPP_VERSION_FLAG: &str = "-std=c++20";
 
 fn main() {
     if std::env::var("DOCS_RS").is_ok() {

rdkit-sys/rustfmt.toml

@@ -48,8 +48,8 @@ trailing_comma = "Vertical"
 match_block_trailing_comma = false
 blank_lines_upper_bound = 1
 blank_lines_lower_bound = 0
-edition = "2021"
-version = "One"
+edition = "2024"
+style_edition = "2024"
 inline_attribute_width = 0
 format_generated_files = true
 merge_derives = true

rdkit-sys/src/bridge/fingerprint.rs

@@ -17,5 +17,24 @@ pub mod ffi {
         pub fn explicit_bit_vect_to_u64_vec(
             bitvect: &SharedPtr<ExplicitBitVect>,
         ) -> UniquePtr<CxxVector<u64>>;
+
+        // Configurable fingerprints
+        pub fn morgan_fingerprint_mol_with_params(
+            mol: &SharedPtr<ROMol>,
+            radius: u32,
+            n_bits: u32,
+        ) -> SharedPtr<ExplicitBitVect>;
+        pub fn rdk_fingerprint_mol_with_params(
+            mol: &SharedPtr<ROMol>,
+            min_path: u32,
+            max_path: u32,
+            fp_size: u32,
+        ) -> SharedPtr<ExplicitBitVect>;
+        pub fn pattern_fingerprint_mol_with_params(
+            mol: &SharedPtr<ROMol>,
+            fp_size: u32,
+        ) -> SharedPtr<ExplicitBitVect>;
+        pub fn maccs_fingerprint_mol(mol: &SharedPtr<ROMol>) -> SharedPtr<ExplicitBitVect>;
+        pub fn explicit_bit_vect_num_bits(bitvect: &SharedPtr<ExplicitBitVect>) -> u32;
     }
 }

rdkit-sys/src/bridge/mod.rs

@@ -11,7 +11,7 @@ mod mol_standardize;
 pub use mol_standardize::ffi as mol_standardize_ffi;
 
 mod periodic_table;
-pub use periodic_table::{ffi as periodic_table_ffi, PeriodicTableOps};
+pub use periodic_table::{PeriodicTableOps, ffi as periodic_table_ffi};
 
 mod ro_mol;
 pub use ro_mol::ffi as ro_mol_ffi;

rdkit-sys/src/bridge/periodic_table.rs

@@ -43,7 +43,7 @@ pub trait PeriodicTableOps {
     fn getElementName(self, atomic_number: u32) -> String;
     fn getValenceList(self, atomic_number: u32) -> &'static CxxVector<i32>;
 }
-impl<'a> PeriodicTableOps for UniquePtr<PeriodicTable> {
+impl PeriodicTableOps for UniquePtr<PeriodicTable> {
     fn getElementSymbol(self, atomic_number: u32) -> String {
         ffi::getElementSymbol(atomic_number)
     }

rdkit-sys/src/bridge/ro_mol.rs

@@ -59,6 +59,7 @@ pub mod ffi {
 
         pub fn get_num_atoms(mol: &SharedPtr<ROMol>, onlyExplicit: bool) -> u32;
         pub fn get_atom_with_idx(mol: &mut SharedPtr<ROMol>, idx: u32) -> Pin<&mut Atom>;
+        pub fn get_atom_with_idx_const(mol: &SharedPtr<ROMol>, idx: u32) -> Pin<&Atom>;
         pub fn get_symbol(atom: Pin<&Atom>) -> String;
         pub fn get_is_aromatic(atom: Pin<&Atom>) -> bool;
         pub fn get_atomic_num(atom: Pin<&Atom>) -> i32;

rdkit-sys/tests/test_atoms.rs

@@ -17,7 +17,9 @@ fn test_atoms() {
 
     assert_eq!(
         &atoms,
-        &["C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C"]
+        &[
+            "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C", "C"
+        ]
     );
 
     let mut atom = rdkit_sys::ro_mol_ffi::get_atom_with_idx(&mut romol, 2);

rdkit-sys/tests/test_ro_mol.rs

@@ -69,7 +69,10 @@ fn mol_to_molblock_test() {
     cxx::let_cxx_string!(smiles = "CC");
     let romol = rdkit_sys::ro_mol_ffi::smiles_to_mol(&smiles).unwrap();
     let molblock = rdkit_sys::ro_mol_ffi::mol_to_molblock(&romol);
-    assert_eq!(molblock, "\n     RDKit          2D\n\n  2  1  0  0  0  0  0  0  0  0999 V2000\n    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n  1  2  1  0\nM  END\n");
+    assert_eq!(
+        molblock,
+        "\n     RDKit          2D\n\n  2  1  0  0  0  0  0  0  0  0999 V2000\n    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n  1  2  1  0\nM  END\n"
+    );
 }
 
 #[test]

rdkit-sys/tests/test_rw_mol.rs

@@ -1,4 +1,4 @@
-use cxx::{let_cxx_string, SharedPtr};
+use cxx::{SharedPtr, let_cxx_string};
 use rdkit_sys::{ro_mol_ffi::ROMol, rw_mol_ffi::RWMol};
 
 #[test]
@@ -191,7 +191,10 @@ CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
     let ro_mol = unsafe { std::mem::transmute::<SharedPtr<RWMol>, SharedPtr<ROMol>>(rw_mol) };
 
     let smiles = rdkit_sys::ro_mol_ffi::mol_to_smiles(&ro_mol);
-    assert_eq!("[H]C([H])([H])C(=O)OC([H])(C([H])([H])C(=O)[O-])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]", &smiles);
+    assert_eq!(
+        "[H]C([H])([H])C(=O)OC([H])(C([H])([H])C(=O)[O-])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]",
+        &smiles
+    );
 }
 
 #[test]

rdkit-sys/wrapper/include/fingerprint.h

@@ -11,4 +11,15 @@ std::shared_ptr<ExplicitBitVect> copy_explicit_bit_vect(const std::shared_ptr<Ex
 unsigned int get_num_on_bits(const std::shared_ptr<ExplicitBitVect> &bitvect);
 
 std::unique_ptr<std::vector<uint64_t>> explicit_bit_vect_to_u64_vec(const std::shared_ptr<ExplicitBitVect> &bitvect);
+
+// Configurable fingerprints
+std::shared_ptr<ExplicitBitVect> morgan_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                    unsigned int radius, unsigned int n_bits);
+std::shared_ptr<ExplicitBitVect> rdk_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                 unsigned int min_path, unsigned int max_path,
+                                                                 unsigned int fp_size);
+std::shared_ptr<ExplicitBitVect> pattern_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                     unsigned int fp_size);
+std::shared_ptr<ExplicitBitVect> maccs_fingerprint_mol(const std::shared_ptr<ROMol> &mol);
+unsigned int explicit_bit_vect_num_bits(const std::shared_ptr<ExplicitBitVect> &bitvect);
 } // namespace RDKit

rdkit-sys/wrapper/include/ro_mol.h

@@ -29,6 +29,8 @@ unsigned int atom_sanitize_exception_get_atom_idx(const MolSanitizeExceptionUniq
 
 unsigned int get_num_atoms(const std::shared_ptr<ROMol> &mol, bool only_explicit);
 Atom &get_atom_with_idx(std::shared_ptr<ROMol> &mol, unsigned int idx);
+const Atom &get_atom_with_idx_const(const std::shared_ptr<ROMol> &mol,
+                                    unsigned int idx);
 rust::String get_symbol(const Atom &atom);
 bool get_is_aromatic(const Atom &atom);
 int get_atomic_num(const Atom &atom);

rdkit-sys/wrapper/src/fingerprint.cc

@@ -1,6 +1,7 @@
 #include "rust/cxx.h"
 #include <DataStructs/ExplicitBitVect.h>
 #include <GraphMol/Fingerprints/Fingerprints.h>
+#include <GraphMol/Fingerprints/MACCS.h>
 #include <GraphMol/Fingerprints/MorganFingerprints.h>
 
 namespace RDKit {
@@ -28,4 +29,28 @@ std::unique_ptr<std::vector<uint64_t>> explicit_bit_vect_to_u64_vec(const std::s
 	std::vector<uint64_t> *bytes_heap = new std::vector<uint64_t>(bytes);
 	return std::unique_ptr<std::vector<uint64_t>>(bytes_heap);
 }
+
+std::shared_ptr<ExplicitBitVect> morgan_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                    unsigned int radius, unsigned int n_bits) {
+	return std::shared_ptr<ExplicitBitVect>(MorganFingerprints::getFingerprintAsBitVect(*mol, radius, n_bits));
+}
+
+std::shared_ptr<ExplicitBitVect> rdk_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                 unsigned int min_path, unsigned int max_path,
+                                                                 unsigned int fp_size) {
+	return std::shared_ptr<ExplicitBitVect>(RDKFingerprintMol(*mol, min_path, max_path, fp_size));
+}
+
+std::shared_ptr<ExplicitBitVect> pattern_fingerprint_mol_with_params(const std::shared_ptr<ROMol> &mol,
+                                                                     unsigned int fp_size) {
+	return std::shared_ptr<ExplicitBitVect>(PatternFingerprintMol(*mol, fp_size));
+}
+
+std::shared_ptr<ExplicitBitVect> maccs_fingerprint_mol(const std::shared_ptr<ROMol> &mol) {
+	return std::shared_ptr<ExplicitBitVect>(MACCSFingerprints::getFingerprintAsBitVect(*mol));
+}
+
+unsigned int explicit_bit_vect_num_bits(const std::shared_ptr<ExplicitBitVect> &bitvect) {
+	return bitvect->getNumBits();
+}
 } // namespace RDKit

rdkit-sys/wrapper/src/ro_mol.cc

@@ -69,6 +69,10 @@ unsigned int get_num_atoms(const std::shared_ptr<ROMol> &mol, bool only_explicit
 
 Atom &get_atom_with_idx(std::shared_ptr<ROMol> &mol, unsigned int idx) { return *mol->getAtomWithIdx(idx); }
 
+const Atom &get_atom_with_idx_const(const std::shared_ptr<ROMol> &mol, unsigned int idx) {
+	return *mol->getAtomWithIdx(idx);
+}
+
 rust::String get_symbol(const Atom &atom) { return atom.getSymbol(); }
 
 bool get_is_aromatic(const Atom &atom) { return atom.getIsAromatic(); }

rustfmt.toml

@@ -48,8 +48,8 @@ trailing_comma = "Vertical"
 match_block_trailing_comma = false
 blank_lines_upper_bound = 1
 blank_lines_lower_bound = 0
-edition = "2021"
-version = "One"
+edition = "2024"
+style_edition = "2024"
 inline_attribute_width = 0
 format_generated_files = true
 merge_derives = true

src/descriptors.rs

@@ -25,7 +25,7 @@ impl Properties {
         let names = rdkit_sys::descriptors_ffi::get_property_names(&self.ptr);
         let computed = rdkit_sys::descriptors_ffi::compute_properties(&self.ptr, &ro_mol.ptr);
 
-        assert!(names.len() != 0);
+        assert!(!names.is_empty());
         assert!(computed.len() == names.len());
 
         names

src/fingerprint.rs

@@ -6,16 +6,26 @@ pub struct Fingerprint(pub BitVec<u8, bitvec::order::Lsb0>);
 
 impl Fingerprint {
     pub fn new(ptr: SharedPtr<rdkit_sys::fingerprint_ffi::ExplicitBitVect>) -> Self {
+        let num_bits = rdkit_sys::fingerprint_ffi::explicit_bit_vect_num_bits(&ptr) as usize;
         let unique_ptr_bytes = rdkit_sys::fingerprint_ffi::explicit_bit_vect_to_u64_vec(&ptr);
         let rdkit_fingerprint_bytes: Vec<u64> = unique_ptr_bytes.into_iter().copied().collect();
         let mut bitvec_u64 = bitvec::vec::BitVec::<u64, Lsb0>::from_vec(rdkit_fingerprint_bytes);
+        bitvec_u64.truncate(num_bits);
 
         let mut idiomatic_bitvec_u8 = bitvec::vec::BitVec::<u8, Lsb0>::new();
         idiomatic_bitvec_u8.append(&mut bitvec_u64);
 
         Fingerprint(idiomatic_bitvec_u8)
     }
 
+    pub fn len(&self) -> usize {
+        self.0.len()
+    }
+
+    pub fn is_empty(&self) -> bool {
+        self.0.is_empty()
+    }
+
     pub fn tanimoto_distance(&self, other: &Fingerprint) -> f32 {
         let and = self.0.clone() & &other.0;
         let or = self.0.clone() | &other.0;